β,3,4-TMPEA

IUPAC: 2-(3,4-Dimethoxyphenyl)-2-methoxyethanamine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: CFEHWNSMGUKJEU-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-13-9-5-4-8(6-10(9)14-2)11(7-12)15-3/h4-6,11H,7,12H2,1-3H3

PubChem CID: 3014315; ChemSpider: 2282798

Shulgin Index: See #49 DMPEA; Table: 4 Page: 330 Row: 11

N-Me-β,3,4-TMPEA

IUPAC: 2-(3,4-Dimethoxyphenyl)-2-methoxy-N-methylethanamine

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: DYEDYZOGYUEUAY-UHFFFAOYSA-N

InChI=1S/C12H19NO3/c1-13-8-12(16-4)9-5-6-10(14-2)11(7-9)15-3/h5-7,12-13H,8H2,1-4H3

PubChem CID: 15612893; ChemSpider: 26711698

Shulgin Index: See #49 DMPEA; Table: 4 Page: 330 Row: 12

N,N-Me-DME
Macromerine
β-Hydroxy-3,4-dimethoxy-N,N-dimethylphenethylamine

IUPAC: 1-(3,4-Dimethoxyphenyl)-2-(dimethylamino)ethanol

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: YAIPYAQVBZPSSC-UHFFFAOYSA-N

InChI=1S/C12H19NO3/c1-13(2)8-10(14)9-5-6-11(15-3)12(7-9)16-4/h5-7,10,14H,8H2,1-4H3

PubChem CID: 165055; ChemSpider: 144706; Wikipedia: Macromerine

Shulgin Index: See #49 DMPEA; Table: 4 Page: 330 Row: 10

Hodgkins, JE; Brown, SD; Massingill, JL. Two new alkaloids in cacti. Tetrahedron Lett., 1 Jan 1967, 8 (14), 1321–1324. 202 kB. doi:10.1016/S0040-4039(00)90694-4

N,N-Me-DMPEA

IUPAC: 2-(3,4-Dimethoxyphenyl)-N,N-dimethylethanamine

Formula: C12H19NO2 Molecular weight: 209.28476 g/mol InChI Key: UNASPKKHQRCVGR-UHFFFAOYSA-N

InChI=1S/C12H19NO2/c1-13(2)8-7-10-5-6-11(14-3)12(9-10)15-4/h5-6,9H,7-8H2,1-4H3

PubChem CID: 355506; ChemSpider: 315575

Shulgin Index: See #49 DMPEA; Table: 4 Page: 330 Row: 15

Ghosal, S; Srivastava, RS. β-Phenethylamine, tetrahydroisoquinoline and indole alkaloids of Desmodium tiliaefolium. Phytochem., 1 Jan 1973, 12 (1), 193–197. 552 kB. doi:10.1016/S0031-9422(00)84646-4

BO3MDM

IUPAC: 2-Methoxy-2-(3-methoxyphenyl)-N,N-dimethylethanamine

Formula: C12H19NO2 Molecular weight: 209.28476 g/mol InChI Key: FFFYOBPHSAESCX-UHFFFAOYSA-N

InChI=1S/C12H19NO2/c1-13(2)9-12(15-4)10-6-5-7-11(8-10)14-3/h5-8,12H,9H2,1-4H3

Shulgin Index: See #101 3-MPEA; Table: 3 Page: 321 Row: 20

Methyleugenol
3,4-Dimethoxyphenylprop-2-ene

IUPAC: 1,2-Dimethoxy-4-(prop-2-en-1-yl)benzene

Formula: C11H14O2 Molecular weight: 178.22766 g/mol InChI Key: ZYEMGPIYFIJGTP-UHFFFAOYSA-N Properties: Essential oil

InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4,6-8H,1,5H2,2-3H3

PubChem CID: 7127; ChemSpider: 21106140; Wikipedia: Eugenol

Shulgin, AT. The separation and identification of the components of the aromatic ether fraction of essential oils by gas-liquid chromatography. J. Chromatogr., 1 Jan 1967, 30, 54–61. 769 kB. doi:10.1016/S0021-9673(00)84112-6

Shulgin, AT; Sargent, T; Naranjo, C. The chemistry and psychopharmacology of nutmeg and of several related phenylisopropylamines. In Ethnopharmacologic Search for Psychoactive Drugs; Efron, DH; Holmstedt, B; Kline, NS, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 28 Jan 1967; pp 202–215. 951 kB.

Nichols, DE; Mason, DL; Jacobsen, LB. Allylbenzene analogs of Δ9-tetrahydrocannabinol as tumor growth inhibitors. Life Sci., 1 Nov 1977, 21 (9), 1245–1247. 150 kB. doi:10.1016/0024-3205(77)90004-2

cis-3,4-Dimethoxyphenylprop-1-ene

IUPAC: 1,2-Dimethoxy-4-[(1Z)-prop-1-en-1-yl]benzene

Formula: C11H14O2 Molecular weight: 178.22766 g/mol InChI Key: NNWHUJCUHAELCL-PLNGDYQASA-N Properties: Essential oil

InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4-8H,1-3H3/b5-4-

PubChem CID: 1549045; ChemSpider: 21242881

Shulgin, AT. The separation and identification of the components of the aromatic ether fraction of essential oils by gas-liquid chromatography. J. Chromatogr., 1 Jan 1967, 30, 54–61. 769 kB. doi:10.1016/S0021-9673(00)84112-6

Methylisoeugenol
trans-3,4-Dimethoxyphenylprop-1-ene

IUPAC: 1,2-Dimethoxy-4-[(1E)-prop-1-en-1-yl]benzene

Formula: C11H14O2 Molecular weight: 178.22766 g/mol InChI Key: NNWHUJCUHAELCL-SNAWJCMRSA-N Properties: Essential oil

InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4-8H,1-3H3/b5-4+

PubChem CID: 637776; ChemSpider: 553362

Shulgin, AT. Composition of the myristicin fraction from oil of nutmeg. Nature, 1 Jan 1963, 197, 379. 107 kB. doi:10.1038/197379a0 Rhodium.

Shulgin, AT. The separation and identification of the components of the aromatic ether fraction of essential oils by gas-liquid chromatography. J. Chromatogr., 1 Jan 1967, 30, 54–61. 769 kB. doi:10.1016/S0021-9673(00)84112-6

Shulgin, AT; Sargent, T; Naranjo, C. The chemistry and psychopharmacology of nutmeg and of several related phenylisopropylamines. In Ethnopharmacologic Search for Psychoactive Drugs; Efron, DH; Holmstedt, B; Kline, NS, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 28 Jan 1967; pp 202–215. 951 kB.

3,4-DMCPA

IUPAC: 2-(3,4-Dimethoxyphenyl)cyclopropanamine

Formula: C11H15NO2 Molecular weight: 193.2423 g/mol InChI Key: XHUGSONRPJURKN-UHFFFAOYSA-N

InChI=1S/C11H15NO2/c1-13-10-4-3-7(5-11(10)14-2)8-6-9(8)12/h3-5,8-9H,6,12H2,1-2H3

PubChem CID: 13972273; ChemSpider: 24205354

Shulgin Index: See #41 DMCPA; Table: 4 Page: 330 Row: 18

Zirkle, CL; Kaiser, C; Tedeschi, DH; Tedeschi, RE; Burger, A. 2-Substituted cyclopropylamines. II. Effect of structure upon monoamine oxidase-inhibitory activity as measured in vivo by potentiation of tryptamine convulsions. J. Med. Chem., 1 Nov 1962, 5 (6), 1265–1284. 1069 kB. doi:10.1021/jm01241a018

AEM
α-Ethylmescaline
α-Ethyl-3,4,5-trimethoxyphenethylamine
2-Amino-1-(3,4,5-trimethoxyphenyl)butane
1-(3,4,5-Trimethoxyphenyl)-2-aminobutane

IUPAC: 1-(3,4,5-Trimethoxyphenyl)butan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: DCYONQVUAUEKAJ-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-5-10(14)6-9-7-11(15-2)13(17-4)12(8-9)16-3/h7-8,10H,5-6,14H2,1-4H3

PubChem CID: 204932; ChemSpider: 177522; Wikipedia: AEM (psychedelic)

Shulgin Index: #1 AEM; Table: 5 Page: 350 Row: 11

Shulgin, AT. Psychotomimetic agents related to mescaline. Experientia, 1 Jan 1963, 19 (3), 127–128. 264 kB. doi:10.1007/BF02171586

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

ASB
Asymbescaline
3,4-Diethoxy-5-methoxyphenethylamine

IUPAC: 2-(3,4-Diethoxy-5-methoxyphenyl)ethanamine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: VFOAVFQWZYUFQZ-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-4-16-12-9-10(6-7-14)8-11(15-3)13(12)17-5-2/h8-9H,4-7,14H2,1-3H3

PubChem CID: 45367; ChemSpider: 41279; Wikipedia: Asymbescaline

Shulgin Index: #8 ASB; Table: 5 Page: 351 Row: 2, #8 ASB; Table: 5 Page: 351 Row: 36

Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1

Jacob, P; Shulgin, AT. Sulfur analogues of psychotomimetic agents. 3. Ethyl homologues of mescaline and their monothioanalogues. J. Med. Chem., 1 Jan 1984, 27 (7), 881–887. 1213 kB. doi:10.1021/jm00373a013

3C-E
4-Ethoxy-3,5-dimethoxyamphetamine
3,5-Dimethoxy-4-ethoxyamphetamine

IUPAC: 1-(4-Ethoxy-3,5-dimethoxyphenyl)propan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: AHLXCGRWNKUNTQ-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-5-17-13-11(15-3)7-10(6-9(2)14)8-12(13)16-4/h7-9H,5-6,14H2,1-4H3

PubChem CID: 44350137; ChemSpider: 21106237; Wikipedia: 3C-E

Shulgin Index: See #117 TMA; Table: 5 Page: 351 Row: 1

2C-O-4
4-Isopropoxy-2,5-dimethoxyphenethylamine
2,5-Dimethoxy-4-isopropoxyphenethylamine

IUPAC: 2-[2,5-Dimethoxy-4-(propan-2-yloxy)phenyl]ethanamine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: KAKXJLWAEMHHTL-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(2)17-13-8-11(15-3)10(5-6-14)7-12(13)16-4/h7-9H,5-6,14H2,1-4H3

PubChem CID: 44719510; ChemSpider: 21106225; Wikipedia: 2C-O-4

Shulgin Index: See #124 TMPEA-2; Table: 5 Page: 345 Row: 5

EMM
2-Ethoxy-4,5-dimethoxyamphetamine
4,5-Dimethoxy-2-ethoxyamphetamine

IUPAC: 1-(2-Ethoxy-4,5-dimethoxyphenyl)propan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: SKRNTJDDBVAEGB-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-5-17-11-8-13(16-4)12(15-3)7-10(11)6-9(2)14/h7-9H,5-6,14H2,1-4H3

PubChem CID: 44719565; ChemSpider: 21106299; Wikipedia: EMM (psychedelic)

Shulgin Index: See #118 TMA-2; Table: 5 Page: 344 Row: 28

Shulgin, AT. The ethyl homologs of 2,4,5-trimethoxyphenylisopropylamine. J. Med. Chem., 1 Jan 1968, 11 (1), 186–187. 242 kB. doi:10.1021/jm00307a056

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 21–41. 8647 kB.

IP
Isoproscaline
3,5-Dimethoxy-4-isopropoxyphenethylamine

IUPAC: 2-[3,5-Dimethoxy-4-(propan-2-yloxy)phenyl]ethanamine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: UBNHYNYMUORHAM-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(2)17-13-11(15-3)7-10(5-6-14)8-12(13)16-4/h7-9H,5-6,14H2,1-4H3

PubChem CID: 15102787; ChemSpider: 10439597; Wikipedia: Isoproscaline

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 13

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413

Nichols, DE; Dyer, DC. Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogues. J. Med. Chem., 1 Jan 1977, 20 (2), 299–301. 409 kB. doi:10.1021/jm00212a022

Nichols, DE; Shulgin, AT; Dyer, DC. Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives. Life Sci., 1 Jan 1977, 21 (4), 569–576. 320 kB.

MEM
2,5-Dimethoxy-4-ethoxyamphetamine

IUPAC: 1-(4-Ethoxy-2,5-dimethoxyphenyl)propan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: ITZLAXJQDMGDEO-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-5-17-13-8-11(15-3)10(6-9(2)14)7-12(13)16-4/h7-9H,5-6,14H2,1-4H3

PubChem CID: 542053; ChemSpider: 472023; Wikipedia: 2,5-Dimethoxy-4-ethoxyamphetamine

Shulgin Index: #87 MEM; Table: 5 Page: 344 Row: 32

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

Shulgin, AT. The ethyl homologs of 2,4,5-trimethoxyphenylisopropylamine. J. Med. Chem., 1 Jan 1968, 11 (1), 186–187. 242 kB. doi:10.1021/jm00307a056

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

Ray, TS. Psychedelics and the human receptorome. PLoS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019

Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 21–41. 8647 kB.

MME
2,4-Dimethoxy-5-ethoxyamphetamine

IUPAC: 1-(5-Ethoxy-2,4-dimethoxyphenyl)propan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: NAMNXRTWJMASNT-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-5-17-13-7-10(6-9(2)14)11(15-3)8-12(13)16-4/h7-9H,5-6,14H2,1-4H3

PubChem CID: 44719602; ChemSpider: 21106338; Wikipedia: MME (psychedelic)

Shulgin Index: See #118 TMA-2; Table: 5 Page: 346 Row: 26

Shulgin, AT. The ethyl homologs of 2,4,5-trimethoxyphenylisopropylamine. J. Med. Chem., 1 Jan 1968, 11 (1), 186–187. 242 kB. doi:10.1021/jm00307a056

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi:10.1038/221537a0

Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 21–41. 8647 kB.

MP
Metaproscaline
3,4-Dimethoxy-5-propoxyphenethylamine
3,4-Dimethoxy-5-n-propoxyphenethylamine

IUPAC: 2-(3,4-Dimethoxy-5-propoxyphenyl)ethanamine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: LRMHEQAATQTVRI-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-4-7-17-12-9-10(5-6-14)8-11(15-2)13(12)16-3/h8-9H,4-7,14H2,1-3H3

PubChem CID: 44375097; ChemSpider: 21106345; Wikipedia: Metaproscaline

Shulgin Index: See #91 Mescaline; Table: 5 Page: 352 Row: 5

Jacob, P; Shulgin, AT. Sulfur analogues of psychotomimetic agents. 3. Ethyl homologues of mescaline and their monothioanalogues. J. Med. Chem., 1 Jan 1984, 27 (7), 881–887. 1213 kB. doi:10.1021/jm00373a013

P
Proscaline
Proscaline
3,5-Dimethoxy-4-propoxyphenethylamine
3,5-Dimethoxy-4-n-propoxyphenethylamine

IUPAC: 2-(3,5-Dimethoxy-4-propoxyphenyl)ethanamine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: HYWLMSUAZVDUFW-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-4-7-17-13-11(15-2)8-10(5-6-14)9-12(13)16-3/h8-9H,4-7,14H2,1-3H3

PubChem CID: 15102790; ChemSpider: 10439596; Wikipedia: Proscaline

Shulgin Index: #104 Proscaline; Table: 5 Page: 351 Row: 11

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 13 Dec 2011. 1038 kB. doi:10.1002/dta.413

Glennon, RA; Kier, LB; Shulgin, AT. Molecular connectivity analysis of hallucinogenic mescaline analogs. J. Pharm. Sci., 1 Jan 1979, 68 (7), 906–907. 252 kB. doi:10.1002/jps.2600680733

Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1

Nichols, DE; Dyer, DC. Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogues. J. Med. Chem., 1 Jan 1977, 20 (2), 299–301. 409 kB. doi:10.1021/jm00212a022

Jacob, P; Shulgin, AT. Sulfur analogues of psychotomimetic agents. 3. Ethyl homologues of mescaline and their monothioanalogues. J. Med. Chem., 1 Jan 1984, 27 (7), 881–887. 1213 kB. doi:10.1021/jm00373a013

Nichols, DE; Shulgin, AT; Dyer, DC. Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives. Life Sci., 1 Jan 1977, 21 (4), 569–576. 320 kB.

Meyers-Riggs, B. Leminger’s scalines. countyourculture: rational exploration of the underground, 4 May 2012.

SB
Symbescaline
3,5-Diethoxy-4-methoxyphenethylamine

IUPAC: 2-(3,5-Diethoxy-4-methoxyphenyl)ethanamine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: ROKMKYBLAPLLER-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-4-16-11-8-10(6-7-14)9-12(17-5-2)13(11)15-3/h8-9H,4-7,14H2,1-3H3

PubChem CID: 44374890; ChemSpider: 21106384; Wikipedia: Symbescaline

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 33

Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. doi:10.1016/S0968-0896(03)00437-1

Jacob, P; Shulgin, AT. Sulfur analogues of psychotomimetic agents. 3. Ethyl homologues of mescaline and their monothioanalogues. J. Med. Chem., 1 Jan 1984, 27 (7), 881–887. 1213 kB. doi:10.1021/jm00373a013

1-(2,5-Dimethoxy-4-methylphenyl)-N-hydroxy-2-aminobutane

IUPAC: 1-(2,5-Dimethoxy-4-methylphenyl)-N-hydroxybutan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: IODVUUDTFABAJR-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-5-11(14-15)7-10-8-12(16-3)9(2)6-13(10)17-4/h6,8,11,14-15H,5,7H2,1-4H3

4C-TMPEA-6
1-(2,4,6-Trimethoxyphenyl)-2-aminobutane

IUPAC: 1-(2,4,6-Trimethoxyphenyl)butan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: RPZWJHJIKUKWKO-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-5-9(14)6-11-12(16-3)7-10(15-2)8-13(11)17-4/h7-9H,5-6,14H2,1-4H3

PubChem CID: 43565966

Shulgin Index: See #122 TMA-6; Table: 5 Page: 353 Row: 28

BOED
2,5-Dimethoxy-β-ethoxy-4-methylphenethylamine

IUPAC: 2-(2,5-Dimethoxy-4-methylphenyl)-2-ethoxyethanamine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: LZNFMACBNUDNGO-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-5-17-13(8-14)10-7-11(15-3)9(2)6-12(10)16-4/h6-7,13H,5,8,14H2,1-4H3

Coutts, RT; Malicky, JL. The synthesis of analogs of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM). II. Some ring-methoxylated 1-amino- and 2-aminoindanes. Can. J. Chem., 1 Feb 1974, 52 (3), 381–389. 615 kB. doi:10.1139/v74-061

Z-7.2
4-Methyl-2,3,6-trimethoxyamphetamine

IUPAC: 1-(2,3,6-Trimethoxy-4-methylphenyl)propan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: OIVHGEYWNKYFLE-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-8-6-11(15-3)10(7-9(2)14)13(17-5)12(8)16-4/h6,9H,7,14H2,1-5H3

Trichocerine
Trichocereine
N,N-Dimethylmescaline
N,N-Dimethyl-3,4,5-trimethoxyphenethylamine

IUPAC: N,N-Dimethyl-2-(3,4,5-trimethoxyphenyl)ethanamine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: BTSKBPJWJZFTPQ-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-14(2)7-6-10-8-11(15-3)13(17-5)12(9-10)16-4/h8-9H,6-7H2,1-5H3

PubChem CID: 420418; ChemSpider: 372161

Shulgin Index: #125 Trichocereine; Table: 5 Page: 350 Row: 25

N-Me-TMA
METHYL-TMA
N-Methyl-3,4,5-trimethoxyamphetamine

IUPAC: N-Methyl-1-(3,4,5-trimethoxyphenyl)propan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: XYKHBBWJSFSLRF-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(14-2)6-10-7-11(15-3)13(17-5)12(8-10)16-4/h7-9,14H,6H2,1-5H3

PubChem CID: 24257271; ChemSpider: 23900079

Shulgin Index: See #117 TMA; Table: 5 Page: 350 Row: 2

N-Me-TMA-2
METHYL-TMA-2
N-Methyl-2,4,5-trimethoxyamphetamine

IUPAC: N-Methyl-1-(2,4,5-trimethoxyphenyl)propan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: USTLBRBKMWJINX-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(14-2)6-10-7-12(16-4)13(17-5)8-11(10)15-3/h7-9,14H,6H2,1-5H3

PubChem CID: 69454104

Shulgin Index: See #118 TMA-2; Table: 5 Page: 344 Row: 24

N-Me-TMA-6
METHYL-TMA-6
N-Methyl-2,4,6-trimethoxyamphetamine

IUPAC: N-Methyl-1-(2,4,6-trimethoxyphenyl)propan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: VSIUFWGLSWJBHU-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(14-2)6-11-12(16-4)7-10(15-3)8-13(11)17-5/h7-9,14H,6H2,1-5H3

PubChem CID: 69393054

Shulgin Index: See #122 TMA-6; Table: 5 Page: 353 Row: 27

2C-O-7
2C-O-7
2,5-Dimethoxy-4-n-propoxyphenethylamine

IUPAC: 2-(2,5-Dimethoxy-4-propoxyphenyl)ethanamine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: RRKXVAQJHSSQHK-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-4-7-17-13-9-11(15-2)10(5-6-14)8-12(13)16-3/h8-9H,4-7,14H2,1-3H3

PubChem CID: 57474252

Shulgin Index: See #124 TMPEA-2; Table: 5 Page: 344 Row: 35

Salbutamol
N-tert-Butyl-β,4-dihydroxy-3-(hydroxymethyl)phenethylamine

IUPAC: 4-[2-(tert-Butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: NDAUXUAQIAJITI-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-13(2,3)14-7-12(17)9-4-5-11(16)10(6-9)8-15/h4-6,12,14-17H,7-8H2,1-3H3

PubChem CID: 2083; ChemSpider: 1999; Wikipedia: Salbutamol

homo-TMA-2

IUPAC: 4-(2,4,5-Trimethoxyphenyl)butan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: PDUFRZLKPVMEJH-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(14)5-6-10-7-12(16-3)13(17-4)8-11(10)15-2/h7-9H,5-6,14H2,1-4H3

PubChem CID: 3839009; ChemSpider: 3064644

Shulgin Index: See #91 Mescaline; Table: 10 Page: 358 Row: 27

homo-TMA-3

IUPAC: 4-(2,3,4-Trimethoxyphenyl)butan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: JZNQOQZDPWRYGP-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(14)5-6-10-7-8-11(15-2)13(17-4)12(10)16-3/h7-9H,5-6,14H2,1-4H3

PubChem CID: 3041182; ChemSpider: 2304487

Shulgin Index: See #91 Mescaline; Table: 10 Page: 358 Row: 29

homo-TMA-6

IUPAC: 4-(2,4,6-Trimethoxyphenyl)butan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: XCOSLSXZEMZDEY-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(14)5-6-11-12(16-3)7-10(15-2)8-13(11)17-4/h7-9H,5-6,14H2,1-4H3

PubChem CID: 3041180; ChemSpider: 2304485

Shulgin Index: See #91 Mescaline; Table: 10 Page: 358 Row: 30

β-HO-β,N,N-Me-2,5-DMPEA

IUPAC: 2-(2,5-Dimethoxyphenyl)-1-(dimethylamino)propan-2-ol

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: NDKCLAODTZQRKW-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-13(15,9-14(2)3)11-8-10(16-4)6-7-12(11)17-5/h6-8,15H,9H2,1-5H3

PubChem CID: 50632; ChemSpider: 45892

Shulgin Index: See #22 2C-H; Table: 4 Page: 335 Row: 20

β-HO-N,N-Me-2,5-DMA

IUPAC: 1-(2,5-Dimethoxyphenyl)-2-(dimethylamino)propan-1-ol

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: IGNNPUVUCCOGBL-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(14(2)3)13(15)11-8-10(16-4)6-7-12(11)17-5/h6-9,13,15H,1-5H3

PubChem CID: 46240; ChemSpider: 42098

Shulgin Index: See #36 2,5-DMA; Table: 4 Page: 335 Row: 28

β-HO-N-Me-2,5-DEPEA

IUPAC: 1-(2,5-Diethoxyphenyl)-2-(methylamino)ethanol

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: ZTNAVFBSHZSJTJ-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-4-16-10-6-7-13(17-5-2)11(8-10)12(15)9-14-3/h6-8,12,14-15H,4-5,9H2,1-3H3

Shulgin Index: See #22 2C-H; Table: 4 Page: 336 Row: 13

β-HO-2,5-DEA

IUPAC: 2-Amino-1-(2,5-diethoxyphenyl)propan-1-ol

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: BGSGDJXRVUYFFR-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-4-16-10-6-7-12(17-5-2)11(8-10)13(15)9(3)14/h6-9,13,15H,4-5,14H2,1-3H3

PubChem CID: 11253430; ChemSpider: 9428457

Shulgin Index: See #36 2,5-DMA; Table: 4 Page: 336 Row: 15

N-Me-TMA-3

IUPAC: N-Methyl-1-(2,3,4-trimethoxyphenyl)propan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: HHLOEWSDUOAEAF-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(14-2)8-10-6-7-11(15-3)13(17-5)12(10)16-4/h6-7,9,14H,8H2,1-5H3

ChemSpider: 21476716

Shulgin Index: See #119 TMA-3; Table: 5 Page: 338 Row: 16

4C-TMPEA-3

IUPAC: 1-(2,3,4-Trimethoxyphenyl)butan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: QMRNVOUMUIECKP-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-5-10(14)8-9-6-7-11(15-2)13(17-4)12(9)16-3/h6-7,10H,5,8,14H2,1-4H3

PubChem CID: 43566032

Shulgin Index: See #119 TMA-3; Table: 5 Page: 338 Row: 17

4C-HM

IUPAC: 4-(2-Aminobutyl)-2,5-dimethoxybenzaldehyde

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: SHHGHSUAGKMYFL-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-4-11(14)5-9-6-13(17-3)10(8-15)7-12(9)16-2/h6-7,11,15H,4-5,8,14H2,1-3H3

PubChem CID: 20315288

Shulgin Index: See #118 TMA-2; Table: 5 Page: 343 Row: 5

BOE

IUPAC: 2-(4-Ethyl-2,5-dimethoxyphenyl)-2-methoxyethanamine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: IJTKRVQOZAXRFT-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-5-9-6-12(16-3)10(7-11(9)15-2)13(8-14)17-4/h6-7,13H,5,8,14H2,1-4H3

PubChem CID: 10331826; ChemSpider: 8507286

Shulgin Index: See #14 BOB; Table: 5 Page: 343 Row: 12

Torres, MA; Cassels, B; Rezende, MC. The preparation of potentially psychoactive β-alkoxyphenethylamines. Synth. Commun., 1 Jan 1995, 25 (8), 1239–1247. 415 kB. doi:10.1080/00397919508012687

DOEH

IUPAC: 2-[4-(2-Aminopropyl)-2,5-dimethoxyphenyl]ethanol

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: XXLDJSGSZKURAM-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(14)6-11-8-12(16-2)10(4-5-15)7-13(11)17-3/h7-9,15H,4-6,14H2,1-3H3

PubChem CID: 14201978; ChemSpider: 21415075

Shulgin Index: See #60 DOM; Table: 5 Page: 343 Row: 25

4C-MeO

IUPAC: 1-(2,4,5-Trimethoxyphenyl)butan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: AJLCTEZQDLTABS-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-5-10(14)6-9-7-12(16-3)13(17-4)8-11(9)15-2/h7-8,10H,5-6,14H2,1-4H3

PubChem CID: 43566022

Shulgin Index: See #118 TMA-2; Table: 5 Page: 344 Row: 27

DESMETHYL-iPr

IUPAC: 2,6-Dimethoxy-4-[2-(propan-2-ylamino)ethyl]phenol

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: MQVBLDXCDVGWQB-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(2)14-6-5-10-7-11(16-3)13(15)12(8-10)17-4/h7-9,14-15H,5-6H2,1-4H3

Shulgin Index: See #29 DESMETHYL; Table: 5 Page: 349 Row: 20

α-MM-M

IUPAC: 2-Methyl-1-(3,4,5-trimethoxyphenyl)propan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: XCMXEBPTBOCOFV-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-13(2,14)8-9-6-10(15-3)12(17-5)11(7-9)16-4/h6-7H,8,14H2,1-5H3

PubChem CID: 3029803; ChemSpider: 2295076

Shulgin Index: See #117 TMA; Table: 5 Page: 350 Row: 9

DOMOM

IUPAC: 1-[2,5-Dimethoxy-4-(methoxymethyl)phenyl]propan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: IACSUTUTFQAPTC-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(14)5-10-6-13(17-4)11(8-15-2)7-12(10)16-3/h6-7,9H,5,8,14H2,1-4H3

PubChem CID: 10934687; ChemSpider: 9109923

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B